Ammonium Chloride → (R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

HRID 246119Notes

Reaction equation

HRID 246119 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].[Cl-].[NH4+]>ClCCl>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH3:11])[CH2:9][O:10][S:23]([CH3:22])(=[O:25])=[O:24])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonateYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((R)-2-Hydroxy-1-methyl-ethyl)-carbamic acid tert-butyl ester (0.5 g, 2.85 mmol) was dissolved in dichloromethane (14 ml) and stirred in an ice bath. N,N-diisopropylethylamine (0.75 ml, 4.28 mmol) and then methanesulfonyl chloride (0.27 ml, 3.4 mmol) were slowly added and the reaction was warmed to room temperature over 16 h. Ammonium chloride solution was added to the reaction and it was extracted two times with ethyl acetate. The combined organics were washed with sodium chloride solution and dried over sodium sulfate. Evaporation gave 0.73 g of methanesulfonic acid (R)-2-tert-butoxycarbonylamino-propyl ester as a waxy white solid. 1H NMR (CDCl3) δ: 4.51-4.68 (m, 1H), 4.19-4.28 (m, 1H), 4.11-4.18 (m, 1H), 3.90-4.04 (m, 1H), 3.03 (s, 3H), 1.24 (d, J=6.8 Hz, 3H).

Workup

  1. extractionwas extracted two times with ethyl acetate
  2. washThe combined organics were washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-19275734b0c84c158d1a3dc796f53c11
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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